The Best Road Cycling Routes in Siena - Tuscany
Discover the best road cycling routes in Siena - Tuscany, Italy. Our curated collection includes 14 handpicked road cycling routes, from shorter coffee rides to challenging all-day rides. The region offers hilly terrain, ideal for riders who enjoy rolling landscapes and varied terrain. Each route includes GPX files, detailed elevation profiles, highlighted climbs, and recommended café stops along the way. Browse the cycling routes map below to find your next ride, or use the filters to narrow by distance, elevation, and difficulty.
14 routes
Chianti West
Loop around the Chianti area, that shows you all the beauty of the region while you ride on tarmac. This route is fully paved, no gravel section. For a little detour you can add in the Brolio's Castle (gravel) when you pass through La Madonna.
Exploring Val di Merse
The Val di Merse is considered a hidden gem in the area south of Siena. Starting from Casciano, the first stop is the San Galgano Abbey, a true highlight. The route continues with gentle climbs and descents along secondary roads and nature reserves, offering constant natural scenery.
Eroica loop from Gaiole in Chianti
Gaiole in Chianti is well known in the cycling world as the home of the Eroica. It is a historic reenactment of early cycling: for one day, thousands of riders use vintage bikes, wear 1920s-style clothing, and ride the dusty white roads. This route follows the opening and closing sections of the permanent Eroica course. The climb to Brolio Castle is especially beautiful.
California Dreaming
A classic long ride for cyclists from Siena is heading to the sea. It’s not just a few kilometers away, but the journey is wonderful. The ride is rewarding, and so is the destination: on the coast is La California, a beautiful seaside town and the hometown of one of Italy’s greatest cyclists, Paolo Bettini.
San Gimignano, Volterra & Monteriggioni
A feast of Tuscan hills. The route passes some of the most iconic villages in the provinces of Siena and Pisa, including San Gimignano and Volterra. The climb to Volterra, about 8 kilometers at an average of 5%, is a perfect excuse for a proper Tuscan lunch.
Southern Chianti
Roughly 1/3 of this route is on gravel, which is nicely spread over the entire ride. In the southern part of the route you'll find some sections that are also included in the Strade Bianche race.
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Plan Your Visit to Siena - Tuscany
Discover where to stay, climbs, routes, bike rentals, cafes, and everything you need to plan your cycling trip in the Siena - Tuscany Guide.